Patent GB-1095902-A (GB)
Title: Guanidine derivatives
IPC: A61Q5/00
Filed: 1965-04-08
Abstract: The invention comprises compounds of the formula <FORM:1095902/C2/1> in which R denotes an alkyl radical of 6-16 carbon atoms or a radical alkyl-Y-alkylene, in which Y is oxygen or sulphur and the alkyl and alkylene groups together contain 3-15 carbon atoms, R1 denotes hydrogen or an alkyl radical of 1-6 carbon atoms, x is 1 or 2 and A denotes any of the following bridging groups:  (1) an alkylene group of 2-12 carbon atoms; (2) a group -(CH2)m-Y-(CH2)n-, in which m and n denote integers from 2 to 6; (3) a group <FORM:1095902/C2/2> (4) a group <FORM:1095902/C2/3> in which Z and Z1 are each alkylene of 1-3 carbon atoms; (5) a group <FORM:1095902/C2/4> in which Q denotes -O-, -S-, -SO- or -SO2-; (6) a diphenyl residue; or (7) a stilbene residue.  A number of groups which A and R may denote are specified. The compounds in which x is 2 (bisbiguanides) may be prepared (1) by reacting a bridged bis-(3-cyanoguanidine) of the formula NC-NH-C(:NH)-NH-A-NH-C(:NH)-NH-CN (or an amidino-O-alkylurea equivalent thereof) with an amine R(R1)NH in salt form; or (2) by reacting a diamine H2N-A-NH2, optionally in salt form, with a 1-alkyl-3-cyanoguanidine of the formula R-N(R1)-C(:NH)-NH-CN. The compounds in which x is 1 (bisguanidines) may be prepared by reacting an appropriate N-alkyl-S-alkylisothiuronium halide with an appropriate bridged diamine.  The products form mono- and di-acid salts with inorganic or organic acids, including mono- or di-carboxylic, sulphonic, sulphinic, phosphonic and phosphinic acids, organic acids of arsenic or antimony, acidic phenolic compounds and Lewis acids. A number of suitable acids are specified. The products also form co-ordination complexes with various heavy-metal ions, e.g. those of vanadium, chromium, manganese, cobalt, nickel, copper, zinc, palladium, rhenium and osmium. In typical examples: (1) 1,1-hexamethylene-bis - (3 - cyanoguanidine) and n - hexylamine hydrochloride yield 1,11-hexamethylene-bis [5-hexylbiguanide], (2) p-phenylene diamine and 1 - n - octyl - 3 - cyanoguanidine yield 1,11-(p-phenylene) - bis - [5 - (n - octyl) biguanide; (3) N - hexyl - S - ethylisothiuronium iodide and hexamethylene diamine yield 1,11-hexamethylene - bis - (3 - hexylguanidine).  Other specified products include a cobalt complex of 1,11-hexamethylene - bis - [5 - (2 - ethylhexyl) biguanide], 1,11 - hexamethylene - bis - [5-(2-ethoxyethyl) biguanide], 1,11-hexamethylene-bis - [5 - (3 - isopropylmercaptopropyl) biguanide], 1,11 - thiobis - (p - phenylene) bis - (5-octylbiguanide), 1,11 - sulphinyl bis - (p-phenylene) bis - (5 - octylbiguanide), 1,11-sulphonyl bis - (p - phenylene) bis - (5 - octylbiguanide), 1,11 - (4,41 - stilbene) bis - (5 - octylbiguanide), 1,11 - [1,4 - cyclohexane bis-(methylene)] bis - (3 - hexylguanidine), 1,11-(p,p1 - biphenylene) bis - (3 - hexylguanidine), 1,11 - (2,3,5,6 - tetrachloro - p - xylylene) bis-[5 - (2 - ethylhexyl) biguanide], and 1,11-hexamethylene - [3 - (5 - methylmercaptopentyl)-guanidine]. The products show antibacterial and fungicidal activity (see Division A5).ALSO:As disinfectants, fungicides and skin and hair conditioners, use is made of bisbiguanides and bisguanidines of the formula <FORM:1095902/A5-A6/1> in which x is 1 or 2, R denotes an alkyl radical of 6-16 carbon atoms or a radical alkyl-Y-alkylene, in which Y is oxygen or sulphur and the alkyl and alkylene groups together contain 3-15 carbon atoms, R1 denotes hydrogen or an alkyl radical of 1-6 carbon atoms, and A denotes any of the following bridging groups:-(1) an alkylene group of 2-12 carbon atoms, (2) a group -(CH2)m-Y-(CH2)n-, in which m and n denote integers from 2 to 6, (3) a group <FORM:1095902/A5-A6/2> (4) a group <FORM:1095902/A5-A6/3> in which Z and Z1 are each alkylene of 1-3 carbon atoms, (5) a group <FORM:1095902/A5-A6/4> in which Q denotes -O-, -S-, -SO- or -SO2, (6) a diphenyl residue or (7) a stilbene residue (see Division C2).  The compounds may be used as such or as their mono- or di-addition salts with acids.  Comparative experimental results are given of the use of some of the compounds as bactericides, bacteriostats, fungicides and fungistats, and example 4 describes the treatment of cotton cloth with one of the compounds to impart an anti-bacterial finish thereto.  It is stated also that some of the products are active against influenza virus and that other products have antihelmintic activity.